Boston to New York

Twelve nights and only 500 miles, Boston to New York the long way round, by way of Cape Cod and the Hamptons. Flights, car and hotels are arranged together from the UK with a road book.

Three nights in Boston start it, a city small enough to walk and old enough to be worth it. Then two nights on Cape Cod, reached through Plymouth and Sandwich, with Provincetown at the very tip of the hook. Newport follows, where the Gilded Age mansions sit above the cliff walk and the America’s Cup still colours the harbour.

The best bit is the crossing. The road runs down the Connecticut shore through Mystic and New London, and then the car goes onto a ferry across Long Island Sound, which is a far better way to arrive on Long Island than the expressway. Two nights in the Hamptons follow, with Southampton, Bridgehampton and East Hampton along the way and Montauk at the end of the island. Four nights in New York close the trip.

Every overnight on this route is a named town, which is less common with this operator than it ought to be. One thing to ask about: the page says late autumn and winter departures may be rerouted inland through the Berkshires and the Hudson Valley, which would take out the Cape, Newport, the ferry and the Hamptons, so most of the trip. Worth pinning down before you book. The itinerary is otherwise bespoke and departures are arranged around your dates. It suits anyone who wants New England in summer and a ferry crossing in the middle of it.